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Cinchona alkaloids

Description:

Alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.

Ancestors:

Organic compounds ⮕ Alkaloids and derivatives ⮕ Cinchona alkaloids
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Items 1-12 of 47

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  1. (+)-Cinchonine
      Grade & Purity: 
    • ≥85%
    Cas Number: 118-10-5        EC Number: 204-234-6
    Formula:  C19H22N2O        Molecular Weight: 294.39
    IUPAC Name:  (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
    SMILES:  C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
    InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
    InChI:  InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
    Synonyms: (S)-quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol | GNF-Pf-3189 | NCGC00262542-03 | .alpha.-Quinidine | N...
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  2. Hydroquinidine 4-chlorobenzoate
      Grade & Purity: 
    • ≥98%
    Cas Number: 113162-02-0
    Formula:  C27H29ClN2O3        Molecular Weight: 465
    IUPAC Name:  [(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] 4-chlorobenzoate
    SMILES:  CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)OC(=O)C5=CC=C(C=C5)Cl
    InChIKey: TXVNNFDXQZFMBQ-XHYUFEOFSA-N
    InChI:  InChI=1S/C27H29ClN2O3/c1-3-17-16-30-13-11-19(17)14-25(30)26(33-27(31)18-4-6-20(28)7-5-18)22-10-12-29-24-9-8-21(32-2)15-23(22)24/h4-10,12,15,17,19,25-2show more
    Synonyms: DTXSID90583559 | Hydroquinidine 4-chlorobenzoate, 98% | J-002905 | [(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-...
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  3. (-)-Quinine
      Grade & Purity: 
    • Moligand™
      •
    • for resolution of racemates for synthesis
    Cas Number: 130-95-0        EC Number: 205-003-2
    Formula:  C20H24N2O2        Molecular Weight: 324.42
    IUPAC Name:  (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
    SMILES:  COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
    InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N
    InChI:  InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,1show more
    Synonyms: (9R)-6'-methoxy-8alpha-cinchonan-9-ol | Quinoline alkaloid | Quinsan | (R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2....
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  4. Quinine monohydrochloride dihydrate
      Grade & Purity: 
    • ≥90%
    Cas Number: 6119-47-7        EC Number: 205-001-1        Compound CID:  16211283
    Formula:  C20H24N2O2·HCl·2H2O        Molecular Weight: 396.91
    IUPAC Name:  (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;dihydrate;hydrochloride
    SMILES:  COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.O.O.Cl
    InChIKey: MPQKYZPYCSTMEI-FLZPLBAKSA-N
    InChI:  InChI=1S/C20H24N2O2.ClH.2H2O/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2Hshow more
    Synonyms: AC-6224 | HY-B0433A | S2502 | FEMA NO. 2976, DIHYDRATE- | Quinine.HCl.dihydrate | (-)-Quinine hydrochloride dihydrate...
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  5. (DHQ)₂AQN
      Grade & Purity: 
    • ≥95%
    Cas Number: 176097-24-8
    Formula:  C54H56N4O6        Molecular Weight: 857.05
    IUPAC Name:  1,4-bis[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]anthracene-9,10-dione
    SMILES:  CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)OC5=C6C(=C(C=C5)OC(C7CC8CCN7CC8CC)C9=C1C=C(C=CC1=NC=C9)OC)C(=O)C1=CC=CC=C1C6=O
    InChIKey: ARCFYUDCVYJQRN-KESJXZTCSA-N
    InChI:  InChI=1S/C54H56N4O6/c1-5-31-29-57-23-19-33(31)25-45(57)53(39-17-21-55-43-13-11-35(61-3)27-41(39)43)63-47-15-16-48(50-49(47)51(59)37-9-7-8-10-38(37)52(show more
    Synonyms: A,9R)-10,11-dihydro-6 inverted exclamation marka-methoxycinchonan-9-yl]oxy]-9,10-anthracenedione | AKOS025405186 | 9,...
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  6. Quinidine hydrochloride monohydrate
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 6151-40-2        EC Number: 205-001-1        Compound CID:  16219921
    Formula:  C20H24N2O2·HCl·H2O        Molecular Weight: 378.89
    IUPAC Name:  (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrate;hydrochloride
    SMILES:  COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.O.Cl
    InChIKey: SGVZDMWHXVXUBY-KAIFKDDSSA-N
    InChI:  InChI=1S/C20H24N2O2.ClH.H2O/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;show more
    Synonyms: Quinidine hydrochloride monohydrate|6151-40-2|Quinidine, monohydrochloride, monohydrate|Z1PDY5DB92|Cinchonan-9-ol, 6'...
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  7. Quinine
    Cas Number: 130-95-0        EC Number: 205-003-2
    Formula:  C20H24N2O2        Molecular Weight: 324.42
    IUPAC Name:  (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
    SMILES:  COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
    InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N
    InChI:  InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,1show more
    Synonyms: Quinine|130-95-0|Chinin|Chinine|(-)-Quinine|6'-Methoxycinchonidine|(8S,9R)-Quinine|Qualaquin|Quinine anhydrous|(R)-(-...
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  8. Quinidine Sulfate
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 6591-63-5        EC Number: 200-046-3        Compound CID:  656862
    Formula:  C40H48N4O4.H2SO4.2H2O        Molecular Weight: 782.94
    IUPAC Name:  (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;sulfuric acid;dihydrate
    SMILES:  COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.O.O.OS(=O)(=O)O
    InChIKey: ZHNFLHYOFXQIOW-AHSOWCEXSA-N
    InChI:  InChI=1S/2C20H24N2O2.H2O4S.2H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4;;/h2*3-6,8,11,13-14,19-20,23H,show more
    Synonyms: Quinidine sulfate dihydrate|6591-63-5|Quinidine sulfate|Cin-Quin|Quinidine sulfate hydrate|Quinidex Extentabs|quinidi...
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  9. Hydroquinine
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 522-66-7        EC Number: 208-334-0
    Formula:  C20H26N2O2        Molecular Weight: 326.43
    IUPAC Name:  (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
    SMILES:  CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
    InChIKey: LJOQGZACKSYWCH-WZBLMQSHSA-N
    InChI:  InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-show more
    Synonyms: HYDROQUININE|Dihydroquinine|522-66-7|(1R)-((2S,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol|hydroq...
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  10. Hydroquinidine
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 1435-55-8        EC Number: 215-862-5
    Formula:  C20H26N2O2        Molecular Weight: 326.43
    IUPAC Name:  (S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
    SMILES:  CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
    InChIKey: LJOQGZACKSYWCH-LHHVKLHASA-N
    InChI:  InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-show more
    Synonyms: hydroquinidine|Dihydroquinidine|1435-55-8|Hydroconquinine|Hydroconchinine|Dihydroquinine|(+)-hydroquinidine|(9S)-10,1...
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  11. Euquinine
      Grade & Purity: 
    • ≥98%
    Cas Number: 83-75-0
    Formula:  C23H28N2O4        Molecular Weight: 396.48
    IUPAC Name:  [(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] ethyl carbonate
    SMILES:  CCOC(=O)OC(C1CC2CCN1CC2C=C)C3=C4C=C(C=CC4=NC=C3)OC
    InChIKey: NSBRKSWSLRQPJW-WWLNLUSPSA-N
    InChI:  InChI=1S/C23H28N2O4/c1-4-15-14-25-11-9-16(15)12-21(25)22(29-23(26)28-5-2)18-8-10-24-20-7-6-17(27-3)13-19(18)20/h4,6-8,10,13,15-16,21-22H,1,5,9,11-12,1show more
    Synonyms: quinine ethylcarbonate|EUQUININE|83-75-0|QUININE ETHYL CARBONATE|Aecachinium|Euquinin|Quinine etabonate|DTXSID0045965...
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  12. Ethylhydrocupreine
      Grade & Purity: 
    • ≥98%
    Cas Number: 522-60-1
    Formula:  C21H28N2O2        Molecular Weight: 340.46
    IUPAC Name:  (R)-(6-ethoxyquinolin-4-yl)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol
    SMILES:  CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OCC)O
    InChIKey: SUWZHLCNFQWNPE-LATRNWQMSA-N
    InChI:  InChI=1S/C21H28N2O2/c1-3-14-13-23-10-8-15(14)11-20(23)21(24)17-7-9-22-19-6-5-16(25-4-2)12-18(17)19/h5-7,9,12,14-15,20-21,24H,3-4,8,10-11,13H2,1-2H3/t1show more
    Synonyms: TCMDC-125547 | (S)-(6-Ethoxyquinolin-4-yl)({5-ethyl-1-azabicyclo[2.2.2]octan-2-yl})methanol | (8alpha,9R)-6'-ethoxy-1...
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